Literature DB >> 22083965

A general strategy for the perfluoroalkylation of arenes and arylbromides by using arylboronate esters and [(phen)CuR(F)].

Nichole D Litvinas1, Patrick S Fier, John F Hartwig.   

Abstract

A versatile method for the synthesis of aryl perfluoroalkanes from arenes and aryl bromides is described. Substituted arenes or aryl bromides are converted in situ to an aryl boronate ester that readily undergoes perfluoroalkylation in air with [(phen)CuR(F)]. A broad range of aryl bromide substrates were perfluoroalkylated in good yield for the first time. [(phen)CuCF(3)] is now commercially available and has been prepared on 20 g scale.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Mesh:

Substances:

Year:  2011        PMID: 22083965      PMCID: PMC3324659          DOI: 10.1002/anie.201106668

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  23 in total

1.  Copper-mediated oxidative trifluoromethylation of boronic acids.

Authors:  Lingling Chu; Feng-Ling Qing
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

2.  A novel catalytic process for trifluoromethylation of bromoaromatic compounds.

Authors:  Bhupesh S Samant; George W Kabalka
Journal:  Chem Commun (Camb)       Date:  2011-05-25       Impact factor: 6.222

3.  Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate.

Authors:  Tatsuo Ishiyama; Jun Takagi; Kousaku Ishida; Norio Miyaura; Natia R Anastasi; John F Hartwig
Journal:  J Am Chem Soc       Date:  2002-01-23       Impact factor: 15.419

4.  Pd(II)-catalyzed ortho-trifluoromethylation of arenes using TFA as a promoter.

Authors:  Xisheng Wang; Larry Truesdale; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

5.  Copper-catalyzed arylation of 1H-perfluoroalkanes.

Authors:  Ilya Popov; Sergey Lindeman; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2011-05-31       Impact factor: 15.419

6.  Thermal, catalytic, regiospecific functionalization of alkanes

Authors: 
Journal:  Science       Date:  2000-03-17       Impact factor: 47.728

7.  Innate C-H trifluoromethylation of heterocycles.

Authors:  Yining Ji; Tobias Brueckl; Ryan D Baxter; Yuta Fujiwara; Ian B Seiple; Shun Su; Donna G Blackmond; Phil S Baran
Journal:  Proc Natl Acad Sci U S A       Date:  2011-08-15       Impact factor: 11.205

8.  Copper-catalyzed trifluoromethylation of aryl boronic acids using a CF3+ reagent.

Authors:  Jun Xu; Dong-Fen Luo; Bin Xiao; Zhao-Jing Liu; Tian-Jun Gong; Yao Fu; Lei Liu
Journal:  Chem Commun (Camb)       Date:  2011-03-07       Impact factor: 6.222

9.  Copper-catalyzed trifluoromethylation of aryl and vinyl boronic acids with an electrophilic trifluoromethylating reagent.

Authors:  Tianfei Liu; Qilong Shen
Journal:  Org Lett       Date:  2011-04-07       Impact factor: 6.005

10.  Active trifluoromethylating agents from well-defined Copper(I)-CF3 complexes.

Authors:  Galyna G Dubinina; Hideki Furutachi; David A Vicic
Journal:  J Am Chem Soc       Date:  2008-06-11       Impact factor: 15.419

View more
  18 in total

1.  Merging visible-light photocatalysis and transition-metal catalysis in the copper-catalyzed trifluoromethylation of boronic acids with CF3I.

Authors:  Yingda Ye; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2012-05-24       Impact factor: 15.419

2.  Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters.

Authors:  Alexander M Haydl; John F Hartwig
Journal:  Org Lett       Date:  2019-02-14       Impact factor: 6.005

3.  Iridium-Catalyzed Silylation of C-H Bonds in Unactivated Arenes: A Sterically Encumbered Phenanthroline Ligand Accelerates Catalysis.

Authors:  Caleb Karmel; Zhewei Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2019-04-23       Impact factor: 15.419

4.  Copper-mediated difluoromethylation of aryl and vinyl iodides.

Authors:  Patrick S Fier; John F Hartwig
Journal:  J Am Chem Soc       Date:  2012-03-14       Impact factor: 15.419

5.  Copper-mediated fluorination of aryl iodides.

Authors:  Patrick S Fier; John F Hartwig
Journal:  J Am Chem Soc       Date:  2012-06-22       Impact factor: 15.419

6.  Copper-mediated radical trifluoromethylation of unsaturated potassium organotrifluoroborates.

Authors:  Marc Presset; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  J Org Chem       Date:  2013-11-19       Impact factor: 4.354

7.  Practical method for the Cu-mediated trifluoromethylation of arylboronic acids with CF3 radicals derived from NaSO2CF3 and tert-butyl hydroperoxide (TBHP).

Authors:  Yingda Ye; Stefan A Künzi; Melanie S Sanford
Journal:  Org Lett       Date:  2012-09-17       Impact factor: 6.005

8.  Late-Stage Conversion of a Metabolically Labile Aryl Methyl Ether-Containing Natural Product to Fluoroalkyl Analogues.

Authors:  Jacob P Sorrentino; Brett R Ambler; Ryan A Altman
Journal:  J Org Chem       Date:  2020-03-27       Impact factor: 4.354

9.  Trifluoromethylation of Arylsilanes with [(phen)CuCF3 ].

Authors:  Johannes Morstein; Haiyun Hou; Chen Cheng; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-23       Impact factor: 15.336

Review 10.  Recent advances in transition metal-catalyzed Csp(2)-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation.

Authors:  Grégory Landelle; Armen Panossian; Sergiy Pazenok; Jean-Pierre Vors; Frédéric R Leroux
Journal:  Beilstein J Org Chem       Date:  2013-11-15       Impact factor: 2.883

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.